JPH0826050B2 - ２−クロルエタンホスホン酸ジクロライドの製造方法 - Google Patents
２−クロルエタンホスホン酸ジクロライドの製造方法Info
- Publication number
- JPH0826050B2 JPH0826050B2 JP62213200A JP21320087A JPH0826050B2 JP H0826050 B2 JPH0826050 B2 JP H0826050B2 JP 62213200 A JP62213200 A JP 62213200A JP 21320087 A JP21320087 A JP 21320087A JP H0826050 B2 JPH0826050 B2 JP H0826050B2
- Authority
- JP
- Japan
- Prior art keywords
- thionyl chloride
- reaction
- alkyl
- chloroethanephosphonic acid
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- LOUZURPQCYZSJH-UHFFFAOYSA-N 1-chloro-2-dichlorophosphorylethane Chemical compound ClCCP(Cl)(Cl)=O LOUZURPQCYZSJH-UHFFFAOYSA-N 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 68
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 16
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
- -1 2-chloroethanephosphonic acid ester Chemical class 0.000 claims description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 150000004714 phosphonium salts Chemical class 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 238000010992 reflux Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- MLSZIADXWDYFKM-UHFFFAOYSA-N 1-dichlorophosphorylethene Chemical compound ClP(Cl)(=O)C=C MLSZIADXWDYFKM-UHFFFAOYSA-N 0.000 description 5
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 4
- XXIDKSWYSYEFAG-UHFFFAOYSA-N 1-chloro-2-[2-chloroethoxy(2-chloroethyl)phosphoryl]oxyethane Chemical compound ClCCOP(=O)(CCCl)OCCCl XXIDKSWYSYEFAG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003003 phosphines Chemical group 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 2
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 1
- UJEFFUXIPMMVMH-UHFFFAOYSA-N bis(4-methoxyphenyl)methylphosphane Chemical compound C1=CC(OC)=CC=C1C(P)C1=CC=C(OC)C=C1 UJEFFUXIPMMVMH-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- CGLPPHBMLXLQKG-UHFFFAOYSA-N diphenylphosphanylmethanamine Chemical compound C=1C=CC=CC=1P(CN)C1=CC=CC=C1 CGLPPHBMLXLQKG-UHFFFAOYSA-N 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 1
- GEPJPYNDFSOARB-UHFFFAOYSA-N tris(4-fluorophenyl)phosphane Chemical compound C1=CC(F)=CC=C1P(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 GEPJPYNDFSOARB-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3629579.5 | 1986-08-30 | ||
| DE19863629579 DE3629579A1 (de) | 1986-08-30 | 1986-08-30 | Verfahren zur herstellung von 2-chlorethanphosphonsaeuredichlorid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6368594A JPS6368594A (ja) | 1988-03-28 |
| JPH0826050B2 true JPH0826050B2 (ja) | 1996-03-13 |
Family
ID=6308574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62213200A Expired - Lifetime JPH0826050B2 (ja) | 1986-08-30 | 1987-08-28 | ２−クロルエタンホスホン酸ジクロライドの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4749524A (enrdf_load_stackoverflow) |
| EP (1) | EP0258805B1 (enrdf_load_stackoverflow) |
| JP (1) | JPH0826050B2 (enrdf_load_stackoverflow) |
| KR (1) | KR950008289B1 (enrdf_load_stackoverflow) |
| CA (1) | CA1304404C (enrdf_load_stackoverflow) |
| DE (2) | DE3629579A1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4494940B2 (ja) * | 2004-11-16 | 2010-06-30 | 日本化学工業株式会社 | 塩素原子を含むホスファゼン誘導体の製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE592086A (enrdf_load_stackoverflow) * | 1959-06-20 | |||
| DE1568945C3 (de) * | 1966-12-23 | 1975-10-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung ungesättigter Phosphonsäuredichloride |
| US3890382A (en) * | 1969-10-04 | 1975-06-17 | Bayer Ag | N-substituted (2-chloroethyl) phosphoramide chloride |
| NL168231C (nl) * | 1970-03-28 | 1982-03-16 | Hoechst Ag | Werkwijze voor het bereiden van 2-chloorethaanfosfonzuurdichloride. |
| CS166044B2 (enrdf_load_stackoverflow) * | 1971-06-15 | 1976-01-29 | ||
| SU582259A1 (ru) * | 1976-07-22 | 1977-11-30 | Московский Ордена Ленина И Ордена Трудового Красного Знамени Государственный Педагогический Институт Им.В.И.Ленина | Способ получени дихлорангидридов фосфоновых кислот |
| US4213922A (en) * | 1978-09-20 | 1980-07-22 | Ciba-Geigy Corporation | Process for producing phosphonic acid halides |
| DE3033614A1 (de) * | 1980-09-06 | 1982-04-29 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von vinylphosphonsaeuredichlorid und 2-chlorethanphosphonsaeuredichlorid |
| DE3541627A1 (de) * | 1985-11-26 | 1987-05-27 | Hoechst Ag | Verfahren zur herstellung von phosphonsaeuredichloriden |
-
1986
- 1986-08-30 DE DE19863629579 patent/DE3629579A1/de active Granted
-
1987
- 1987-08-26 DE DE8787112380T patent/DE3773093D1/de not_active Expired - Fee Related
- 1987-08-26 EP EP87112380A patent/EP0258805B1/de not_active Expired - Lifetime
- 1987-08-27 US US07/089,827 patent/US4749524A/en not_active Expired - Fee Related
- 1987-08-28 JP JP62213200A patent/JPH0826050B2/ja not_active Expired - Lifetime
- 1987-08-28 CA CA000545595A patent/CA1304404C/en not_active Expired - Fee Related
- 1987-08-29 KR KR87009492A patent/KR950008289B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6368594A (ja) | 1988-03-28 |
| DE3629579A1 (de) | 1988-03-03 |
| EP0258805B1 (de) | 1991-09-18 |
| KR950008289B1 (en) | 1995-07-27 |
| EP0258805A3 (en) | 1988-08-17 |
| CA1304404C (en) | 1992-06-30 |
| DE3629579C2 (enrdf_load_stackoverflow) | 1989-05-24 |
| EP0258805A2 (de) | 1988-03-09 |
| US4749524A (en) | 1988-06-07 |
| KR880002887A (ko) | 1988-05-12 |
| DE3773093D1 (de) | 1991-10-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2382309A (en) | Phosphonamide | |
| US3808265A (en) | Preparation of 2-haloethylphosphonic acid | |
| US4990642A (en) | Process for preparing oximosilanes | |
| JPH0826050B2 (ja) | ２−クロルエタンホスホン酸ジクロライドの製造方法 | |
| EP0097522A2 (en) | Preparation of N-phosphonomethylglycine | |
| US4307040A (en) | Process for producing phosphonomaleic acid esters | |
| US4246199A (en) | Process for the preparation of N-alkyl-substituted carboxylic acid amides | |
| JPS603318B2 (ja) | 塩化ホスフアイトの製造方法 | |
| US4735748A (en) | Process for making phosphonic acid dichlorides | |
| US4062888A (en) | Continuous production of 2,5-dioxo-1-oxa-2-phospholanes | |
| US4525311A (en) | O,O-Dialkyl-N-(benzyl or t-butyl)-N-cyanomethyl aminomethylphosphonates | |
| JPH072883A (ja) | 亜燐酸アルキルの製造法 | |
| US4761252A (en) | Process for the preparation of vinylphosphonic dichloride | |
| US3681448A (en) | Perfluoro-1-cycloalken-1,2-ylene-diphosphoryl compounds | |
| JPH0826051B2 (ja) | ２−クロロエタンホスホン酸ジクロライドの製造方法 | |
| JPS5850232B2 (ja) | ホスホンサンオヨビ ホスフインサンノ セイホウ | |
| US4481151A (en) | Process for the preparation of dialkylphosphinic acid halides | |
| US4708824A (en) | Process for the preparation of chloro(phenyl)phospines | |
| JP7628947B2 (ja) | マラチオンの触媒による環境に優しい製造方法 | |
| JP2825581B2 (ja) | ４，５，６―トリクロロピリミジンの製造方法 | |
| US3997611A (en) | Production of tertiary phosphine oxides | |
| US4224241A (en) | Production of halogenomethylphosphinic acid halides | |
| JPH0676424B2 (ja) | ２，６―ジアルキルフェノキシジハロホスファイトの製造法 | |
| JPH0415794B2 (enrdf_load_stackoverflow) | ||
| JPS5839157B2 (ja) | リンガンユウエステルノセイホウ |